JP2020536915A5 - - Google Patents
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- Publication number
- JP2020536915A5 JP2020536915A5 JP2020520532A JP2020520532A JP2020536915A5 JP 2020536915 A5 JP2020536915 A5 JP 2020536915A5 JP 2020520532 A JP2020520532 A JP 2020520532A JP 2020520532 A JP2020520532 A JP 2020520532A JP 2020536915 A5 JP2020536915 A5 JP 2020536915A5
- Authority
- JP
- Japan
- Prior art keywords
- fluoro
- phenyl
- triazole
- dihydro
- pyrrolo
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- -1 C 1- C 6 alkyl Chemical group 0.000 claims 40
- 150000001875 compounds Chemical class 0.000 claims 21
- 150000003839 salts Chemical class 0.000 claims 20
- 125000004093 cyano group Chemical group *C#N 0.000 claims 18
- 125000001153 fluoro group Chemical group F* 0.000 claims 18
- 229910052739 hydrogen Inorganic materials 0.000 claims 17
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 15
- 239000001257 hydrogen Substances 0.000 claims 15
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 15
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 11
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 9
- 229910052799 carbon Inorganic materials 0.000 claims 9
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 9
- 208000002320 spinal muscular atrophy Diseases 0.000 claims 9
- 125000001424 substituent group Chemical group 0.000 claims 9
- 125000000623 heterocyclic group Chemical group 0.000 claims 8
- 229910052736 halogen Inorganic materials 0.000 claims 7
- 150000002367 halogens Chemical class 0.000 claims 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 7
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 6
- 206010012289 Dementia Diseases 0.000 claims 6
- 206010033799 Paralysis Diseases 0.000 claims 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 6
- 125000004432 carbon atom Chemical group C* 0.000 claims 6
- 229910052757 nitrogen Inorganic materials 0.000 claims 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 6
- 208000021090 palsy Diseases 0.000 claims 6
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 5
- 239000008194 pharmaceutical composition Substances 0.000 claims 5
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims 4
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 125000004438 haloalkoxy group Chemical group 0.000 claims 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 4
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 3
- 208000024827 Alzheimer disease Diseases 0.000 claims 3
- 206010008111 Cerebral haemorrhage Diseases 0.000 claims 3
- 208000032843 Hemorrhage Diseases 0.000 claims 3
- 208000023105 Huntington disease Diseases 0.000 claims 3
- 208000001089 Multiple system atrophy Diseases 0.000 claims 3
- 208000018737 Parkinson disease Diseases 0.000 claims 3
- 208000032319 Primary lateral sclerosis Diseases 0.000 claims 3
- 208000006011 Stroke Diseases 0.000 claims 3
- 208000034799 Tauopathies Diseases 0.000 claims 3
- 206010046298 Upper motor neurone lesion Diseases 0.000 claims 3
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims 3
- 208000034158 bleeding Diseases 0.000 claims 3
- 230000000740 bleeding effect Effects 0.000 claims 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims 3
- 229910052731 fluorine Inorganic materials 0.000 claims 3
- 125000001072 heteroaryl group Chemical group 0.000 claims 3
- 238000007917 intracranial administration Methods 0.000 claims 3
- 208000028867 ischemia Diseases 0.000 claims 3
- 201000010901 lateral sclerosis Diseases 0.000 claims 3
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 3
- 208000005264 motor neuron disease Diseases 0.000 claims 3
- 201000000585 muscular atrophy Diseases 0.000 claims 3
- 201000006938 muscular dystrophy Diseases 0.000 claims 3
- 208000033808 peripheral neuropathy Diseases 0.000 claims 3
- 230000000750 progressive effect Effects 0.000 claims 3
- 201000008752 progressive muscular atrophy Diseases 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- 208000011580 syndromic disease Diseases 0.000 claims 3
- 230000002123 temporal effect Effects 0.000 claims 3
- KPKUNSHYTZNQGB-STQMWFEESA-N (5S,7S)-2-(2-ethoxyethyl)-7-fluoro-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound CCOCCC1=NN2[C@@H](C[C@H](F)C2=N1)C1=CC=CC=C1 KPKUNSHYTZNQGB-STQMWFEESA-N 0.000 claims 2
- IOASJLGDLUGRAU-KBPBESRZSA-N (5S,7S)-2-(cyclobutylmethyl)-7-fluoro-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound F[C@H]1C[C@H](N2N=C(CC3CCC3)N=C12)C1=CC=CC=C1 IOASJLGDLUGRAU-KBPBESRZSA-N 0.000 claims 2
- ALCTUKGOYARRNH-AVGNSLFASA-N (5S,7S)-2-[(S)-cyclopropyl(fluoro)methyl]-7-fluoro-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound F[C@@H](C1CC1)C1=NN2[C@@H](C[C@H](F)C2=N1)C1=CC=CC=C1 ALCTUKGOYARRNH-AVGNSLFASA-N 0.000 claims 2
- UHAUTGSTWXFJTQ-YWGVVOLTSA-N (5S,7S)-2-[1-bicyclo[1.1.1]pentanyl(difluoro)methyl]-7-fluoro-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound C1=CC=CC=C1[C@H]1N2C([C@H](C1)F)=NC(C(C13CC(C1)C3)(F)F)=N2 UHAUTGSTWXFJTQ-YWGVVOLTSA-N 0.000 claims 2
- JEGJYXYMPWLQOO-RYUDHWBXSA-N (5S,7S)-2-[cyclopropyl(difluoro)methyl]-7-fluoro-5-(2-fluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound F[C@H]1C[C@H](N2N=C(N=C12)C(F)(F)C1CC1)C1=C(F)C=CC=C1 JEGJYXYMPWLQOO-RYUDHWBXSA-N 0.000 claims 2
- MUJRUMLHIAZTAZ-BQUFFADESA-N (5S,7S)-7-fluoro-2-[(1S,2S)-2-methylcyclopropyl]-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound C[C@H]1C[C@@H]1C1=NN2[C@@H](C[C@H](F)C2=N1)C1=CC=CC=C1 MUJRUMLHIAZTAZ-BQUFFADESA-N 0.000 claims 2
- RXUYYIANSGIRBA-STQMWFEESA-N (5S,7S)-7-fluoro-5-phenyl-2-(propan-2-yloxymethyl)-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound CC(C)OCC1=NN2[C@@H](C[C@H](F)C2=N1)C1=CC=CC=C1 RXUYYIANSGIRBA-STQMWFEESA-N 0.000 claims 2
- GDTCUGRIYFPSJN-UHFFFAOYSA-N 2-[(2,2-difluorocyclopropyl)methyl]-7-fluoro-5-(2-fluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound FC1CC(c2ccccc2F)n2nc(CC3CC3(F)F)nc12 GDTCUGRIYFPSJN-UHFFFAOYSA-N 0.000 claims 2
- 208000016192 Demyelinating disease Diseases 0.000 claims 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 2
- 230000002490 cerebral effect Effects 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 230000001054 cortical effect Effects 0.000 claims 2
- 230000007850 degeneration Effects 0.000 claims 2
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 239000001301 oxygen Chemical group 0.000 claims 2
- 201000002212 progressive supranuclear palsy Diseases 0.000 claims 2
- 125000004434 sulfur atom Chemical group 0.000 claims 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 2
- WDRYHJYWUJHCFD-RNJOBUHISA-N (1R,2R)-2-[(5S,7S)-7-fluoro-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazol-2-yl]cyclopropane-1-carbonitrile Chemical compound F[C@H]1C[C@@H](c2ccccc2)n2nc(nc12)[C@@H]1C[C@H]1C#N WDRYHJYWUJHCFD-RNJOBUHISA-N 0.000 claims 1
- FHXFRFFNQZTYIR-IALDZJHCSA-N (1S,2S)-2-[difluoro-(7-fluoro-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazol-2-yl)methyl]cyclopropane-1-carbonitrile Chemical compound FC([C@@H]1[C@H](C1)C#N)(C=1N=C2N(N=1)C(CC2F)C1=CC=CC=C1)F FHXFRFFNQZTYIR-IALDZJHCSA-N 0.000 claims 1
- BKAOETZHKDXDGK-RKDXNWHRSA-N (5R,7R)-2-(difluoromethyl)-7-fluoro-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound FC(F)C1=NN2[C@H](C[C@@H](F)C2=N1)C1=CC=CC=C1 BKAOETZHKDXDGK-RKDXNWHRSA-N 0.000 claims 1
- PMUFTGWGLJZNOX-ZDUSSCGKSA-N (5S)-2-(cyclopropylmethyl)-5-(2-fluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound FC1=C(C=CC=C1)[C@@H]1CCC2=NC(CC3CC3)=NN12 PMUFTGWGLJZNOX-ZDUSSCGKSA-N 0.000 claims 1
- JCPPXNOEDKUSMA-LBPRGKRZSA-N (5S)-5-(2-fluorophenyl)-2-propyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound CCCC1=NN2[C@@H](CCC2=N1)C1=C(F)C=CC=C1 JCPPXNOEDKUSMA-LBPRGKRZSA-N 0.000 claims 1
- VBFUHRXFACWWGQ-DVRYWGNFSA-N (5S,7S)-2-(2,2-difluorocyclopropyl)-7-fluoro-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound F[C@H]1C[C@H](N2N=C(N=C12)C1CC1(F)F)C1=CC=CC=C1 VBFUHRXFACWWGQ-DVRYWGNFSA-N 0.000 claims 1
- WLVQXZPCKIROOP-SPOOISQMSA-N (5S,7S)-2-(2,2-dimethylcyclopropyl)-7-fluoro-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound CC1(C)CC1C1=NN2[C@@H](C[C@H](F)C2=N1)C1=CC=CC=C1 WLVQXZPCKIROOP-SPOOISQMSA-N 0.000 claims 1
- LICTZQWETXXEHP-QWRGUYRKSA-N (5S,7S)-2-(2-chloroimidazol-1-yl)-7-fluoro-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound F[C@H]1C[C@H](N2N=C(N=C12)N1C=CN=C1Cl)C1=CC=CC=C1 LICTZQWETXXEHP-QWRGUYRKSA-N 0.000 claims 1
- CNUBVSIYBTVMDH-KBPBESRZSA-N (5S,7S)-2-(2-cyclopropylethynyl)-7-fluoro-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound F[C@H]1C[C@H](N2N=C(N=C12)C#CC1CC1)C1=CC=CC=C1 CNUBVSIYBTVMDH-KBPBESRZSA-N 0.000 claims 1
- NROHODVQFPILMY-QWRGUYRKSA-N (5S,7S)-2-(3,3-difluoropropyl)-7-fluoro-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound FC(F)CCC1=NN2[C@@H](C[C@H](F)C2=N1)C1=CC=CC=C1 NROHODVQFPILMY-QWRGUYRKSA-N 0.000 claims 1
- CYUQVAGRGYEPQD-KBPBESRZSA-N (5S,7S)-2-(4,5-dimethylimidazol-1-yl)-7-fluoro-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound CC1=C(C)N(C=N1)C1=NN2[C@@H](C[C@H](F)C2=N1)C1=CC=CC=C1 CYUQVAGRGYEPQD-KBPBESRZSA-N 0.000 claims 1
- MSAYVCFDYBZMAP-QWRGUYRKSA-N (5S,7S)-2-(4-chloroimidazol-1-yl)-7-fluoro-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound F[C@H]1C[C@H](N2N=C(N=C12)N1C=NC(Cl)=C1)C1=CC=CC=C1 MSAYVCFDYBZMAP-QWRGUYRKSA-N 0.000 claims 1
- QBKVTLIQUSUQRS-RYUDHWBXSA-N (5S,7S)-2-(4-chloropyrazol-1-yl)-7-fluoro-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound F[C@H]1C[C@H](N2N=C(N=C12)N1C=C(Cl)C=N1)C1=CC=CC=C1 QBKVTLIQUSUQRS-RYUDHWBXSA-N 0.000 claims 1
- FLYMGQORFVCALO-GJZGRUSLSA-N (5S,7S)-2-(4-cyclopropylpyrazol-1-yl)-7-fluoro-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound F[C@H]1C[C@H](N2N=C(N=C12)N1C=C(C=N1)C1CC1)C1=CC=CC=C1 FLYMGQORFVCALO-GJZGRUSLSA-N 0.000 claims 1
- FSNONCHUJMFFJY-KBPBESRZSA-N (5S,7S)-2-(4-ethylpyrazol-1-yl)-7-fluoro-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound CCC1=CN(N=C1)C1=NN2[C@@H](C[C@H](F)C2=N1)C1=CC=CC=C1 FSNONCHUJMFFJY-KBPBESRZSA-N 0.000 claims 1
- YASNUJHAYIJJNC-RAMGSTBQSA-N (5S,7S)-2-[(2,2-difluorocyclopropyl)methyl]-7-fluoro-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound F[C@H]1C[C@H](N2N=C(CC3CC3(F)F)N=C12)C1=CC=CC=C1 YASNUJHAYIJJNC-RAMGSTBQSA-N 0.000 claims 1
- HZAROVNAMRBNGP-CLJTZFLHSA-N (5S,7S)-2-[(R)-1-bicyclo[1.1.1]pentanyl(fluoro)methyl]-7-fluoro-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound C1=CC=CC=C1[C@H]1N2C([C@H](C1)F)=NC([C@@H](C13CC(C1)C3)F)=N2 HZAROVNAMRBNGP-CLJTZFLHSA-N 0.000 claims 1
- ALCTUKGOYARRNH-RWMBFGLXSA-N (5S,7S)-2-[(R)-cyclopropyl(fluoro)methyl]-7-fluoro-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound F[C@H](C1CC1)C1=NN2[C@@H](C[C@H](F)C2=N1)C1=CC=CC=C1 ALCTUKGOYARRNH-RWMBFGLXSA-N 0.000 claims 1
- HZAROVNAMRBNGP-UGLBVFMYSA-N (5S,7S)-2-[(S)-1-bicyclo[1.1.1]pentanyl(fluoro)methyl]-7-fluoro-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound C1=CC=CC=C1[C@H]1N2C([C@@H](F)C1)=NC(=N2)[C@H](C12CC(C1)C2)F HZAROVNAMRBNGP-UGLBVFMYSA-N 0.000 claims 1
- GVXHTMMRYFHKSQ-RYUDHWBXSA-N (5S,7S)-2-[cyclopropyl(difluoro)methyl]-7-fluoro-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound F[C@H]1C[C@H](N2N=C(N=C12)C(F)(F)C1CC1)C1=CC=CC=C1 GVXHTMMRYFHKSQ-RYUDHWBXSA-N 0.000 claims 1
- LTFXUKMFJNTABL-STQMWFEESA-N (5S,7S)-2-but-1-en-2-yl-7-fluoro-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound CCC(=C)C1=NN2[C@@H](C[C@H](F)C2=N1)C1=CC=CC=C1 LTFXUKMFJNTABL-STQMWFEESA-N 0.000 claims 1
- NUZSTKOHEMQTRQ-QWRGUYRKSA-N (5S,7S)-2-ethenyl-7-fluoro-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound F[C@H]1C[C@H](N2N=C(C=C)N=C12)C1=CC=CC=C1 NUZSTKOHEMQTRQ-QWRGUYRKSA-N 0.000 claims 1
- KGPQVYVRXMOVKQ-RYUDHWBXSA-N (5S,7S)-7-fluoro-2-(1-methylimidazol-2-yl)-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound CN1C=CN=C1C1=NN2[C@@H](C[C@H](F)C2=N1)C1=CC=CC=C1 KGPQVYVRXMOVKQ-RYUDHWBXSA-N 0.000 claims 1
- NULLQENWXKEGAA-STQMWFEESA-N (5S,7S)-7-fluoro-2-(2-methylimidazol-1-yl)-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound CC1=NC=CN1C1=NN2[C@@H](C[C@H](F)C2=N1)C1=CC=CC=C1 NULLQENWXKEGAA-STQMWFEESA-N 0.000 claims 1
- ZJSLXLZEVNZLOX-QWRGUYRKSA-N (5S,7S)-7-fluoro-2-(4-fluoroimidazol-1-yl)-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound F[C@H]1C[C@H](N2N=C(N=C12)N1C=NC(F)=C1)C1=CC=CC=C1 ZJSLXLZEVNZLOX-QWRGUYRKSA-N 0.000 claims 1
- PLSQSURQPYGYGM-RYUDHWBXSA-N (5S,7S)-7-fluoro-2-(4-fluoropyrazol-1-yl)-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound F[C@H]1C[C@H](N2N=C(N=C12)N1C=C(F)C=N1)C1=CC=CC=C1 PLSQSURQPYGYGM-RYUDHWBXSA-N 0.000 claims 1
- WCMWOUHEAUMMDL-STQMWFEESA-N (5S,7S)-7-fluoro-2-(4-methoxypyrazol-1-yl)-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound COC1=CN(N=C1)C1=NN2[C@@H](C[C@H](F)C2=N1)C1=CC=CC=C1 WCMWOUHEAUMMDL-STQMWFEESA-N 0.000 claims 1
- RKMIQCIBZJBJTH-STQMWFEESA-N (5S,7S)-7-fluoro-2-(4-methylsulfonylpyrazol-1-yl)-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound CS(=O)(=O)C1=CN(N=C1)C1=NN2[C@@H](C[C@H](F)C2=N1)C1=CC=CC=C1 RKMIQCIBZJBJTH-STQMWFEESA-N 0.000 claims 1
- MIRIPTKIMZOSGE-RYUDHWBXSA-N (5S,7S)-7-fluoro-2-(5-methyl-1,2,4-triazol-1-yl)-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound CC1=NC=NN1C1=NN2[C@@H](C[C@H](F)C2=N1)C1=CC=CC=C1 MIRIPTKIMZOSGE-RYUDHWBXSA-N 0.000 claims 1
- RGTCHMJHRGZKQJ-STQMWFEESA-N (5S,7S)-7-fluoro-2-(5-methylpyrazol-1-yl)-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound CC1=CC=NN1C1=NN2[C@@H](C[C@H](F)C2=N1)C1=CC=CC=C1 RGTCHMJHRGZKQJ-STQMWFEESA-N 0.000 claims 1
- UMJVNPXGZIEYDO-RYUDHWBXSA-N (5S,7S)-7-fluoro-2-imidazol-1-yl-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound F[C@H]1C[C@H](N2N=C(N=C12)N1C=CN=C1)C1=CC=CC=C1 UMJVNPXGZIEYDO-RYUDHWBXSA-N 0.000 claims 1
- GGRANSKWVSEKOT-QWRGUYRKSA-N (5S,7S)-7-fluoro-5-phenyl-2-(1,2,4-triazol-1-yl)-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound F[C@H]1C[C@H](N2N=C(N=C12)N1C=NC=N1)C1=CC=CC=C1 GGRANSKWVSEKOT-QWRGUYRKSA-N 0.000 claims 1
- UNGACTKJXUJRLY-QWRGUYRKSA-N (5S,7S)-7-fluoro-5-phenyl-2-(3,3,3-trifluoropropyl)-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound F[C@H]1C[C@H](N2N=C(CCC(F)(F)F)N=C12)C1=CC=CC=C1 UNGACTKJXUJRLY-QWRGUYRKSA-N 0.000 claims 1
- PCHGYNYQBVSCGW-GJZGRUSLSA-N (5S,7S)-7-fluoro-5-phenyl-2-(4-propan-2-ylpyrazol-1-yl)-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole Chemical compound CC(C)C1=CN(N=C1)C1=NN2[C@@H](C[C@H](F)C2=N1)C1=CC=CC=C1 PCHGYNYQBVSCGW-GJZGRUSLSA-N 0.000 claims 1
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| MX2014013407A (es) | 2012-05-22 | 2014-11-26 | Hoffmann La Roche | Dipiridilaminas sustituidas y uso de las mismas. |
| BR112015016395A2 (pt) | 2013-01-18 | 2017-07-11 | Hoffmann La Roche | pirazóis 3-substituídos e uso como inibidores de dlk |
| TWI638815B (zh) | 2013-02-15 | 2018-10-21 | 英商葛蘭素史克智慧財產發展有限公司 | 作為激酶抑制劑之雜環醯胺類（一） |
| KR20160002850A (ko) | 2013-05-01 | 2016-01-08 | 에프. 호프만-라 로슈 아게 | C-연결된 헤테로사이클로알킬 치환된 피리미딘 및 이의 용도 |
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| JP6701225B2 (ja) | 2015-03-09 | 2020-05-27 | エフ．ホフマン−ラ ロシュ アーゲーＦ． Ｈｏｆｆｍａｎｎ−Ｌａ Ｒｏｃｈｅ Ａｋｔｉｅｎｇｅｓｅｌｌｓｃｈａｆｔ | 三環式ｄｌｋ阻害剤及びその使用 |
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-
2018
- 2018-10-10 EP EP18785936.8A patent/EP3694858B1/en active Active
- 2018-10-10 KR KR1020207013188A patent/KR20200070297A/ko not_active Ceased
- 2018-10-10 CN CN201880066460.0A patent/CN111201229B/zh active Active
- 2018-10-10 MX MX2020003439A patent/MX2020003439A/es unknown
- 2018-10-10 MA MA050356A patent/MA50356A/fr unknown
- 2018-10-10 BR BR112020007067-0A patent/BR112020007067A2/pt not_active Application Discontinuation
- 2018-10-10 AU AU2018348930A patent/AU2018348930A1/en not_active Abandoned
- 2018-10-10 SG SG11202003283TA patent/SG11202003283TA/en unknown
- 2018-10-10 PE PE2020000378A patent/PE20211246A1/es unknown
- 2018-10-10 CA CA3078653A patent/CA3078653A1/en active Pending
- 2018-10-10 CR CR20200151A patent/CR20200151A/es unknown
- 2018-10-10 RU RU2020114670A patent/RU2020114670A/ru unknown
- 2018-10-10 WO PCT/EP2018/077656 patent/WO2019072942A1/en not_active Ceased
- 2018-10-10 JP JP2020520532A patent/JP7362600B2/ja active Active
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2020
- 2020-03-19 IL IL273443A patent/IL273443A/en unknown
- 2020-04-08 CL CL2020000944A patent/CL2020000944A1/es unknown
- 2020-04-09 PH PH12020550253A patent/PH12020550253A1/en unknown
- 2020-04-09 US US16/844,952 patent/US11673892B2/en active Active
- 2020-04-23 CO CONC2020/0004977A patent/CO2020004977A2/es unknown
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